Pyridone dyes

ABSTRACT

Pyridone dyes of the formula ##STR1## where X is nitrogen or C--CN, 
     R 1  and R 2  are each substituted or unsubstituted C 1  -C 10  -alkyl, C 5  -C 7  -cycloalkyl, C 3  -C 4  -alkenyl or substituted or unsubstituted phenyl, or R 1  and R 2  together with the nitrogen atom joining them together are a heterocyclic radical, 
     R 3  is hydrogen, C 1  -C 10  -alkyl, C 4  -C 7  -cylcoalkyl, benzyl, substituted or unsubstituted phenyl, substituted or unsubstituted furanyl or substituted or unsubstituted thienyl, 
     R 4  is hydrogen, C 1  -C 4  -alkyl or substituted or unsubstituted phenyl, 
     R 5  is cyano, carbamoyl, mono- or di(C 1  -C 8  -alkyl)carbamoyl, carboxyl, C 1  -C 8  -alkoxycarbonyl or benzimidazolyl, and 
     R 6  is substituted or unsubstituted C 1  -C 10  -alkyl, C 5  -C 7  -cycloalkyl or substituted or unsubstituted phenyl, 
     are useful for dyeing or printing textile materials.

The present invention relates to novel pyridone dyes of the formula I ##STR2## where

X is nitrogen or C--CN,

R¹ and R² are identical or different and each is independently of the other unsubstituted or C₁ -C₄ -alkoxycarbonyl-, C₁ -C₄ -alkoxycarbonyloxy- or phenyl-substituted C₁ -C₁₀ -alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function, C₅ -C₇ -cycloalkyl, C₃ -C₄ -alkenyl, unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl, or R¹ and R² are together with the nitrogen atom joining them together a 5- or 6-membered saturated heterocyclic radical with or without further hetero atoms,

R³ is hydrogen, C₁ -C₁₀ -alkyl, C₅ -C₇ -cycloalkyl, benzyl, unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl, furanyl or thienyl, the last two radicals being unsubstituted or C₁ -C₄ -alkyl- or halogen-substituted,

R⁴ is hydrogen, C₁ -C₄ -alkyl or unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl,

R⁵ is cyano, carbamoyl, mono- or di(C₁ -C₈ -alkyl)carbamoyl, carboxyl, C₁ -C₈ -alkoxycarbonyl or benzimidazolyl, and

R⁶ is unsubstituted or phenyl-, phenoxy-, cyclohexyloxy- or pyrazolyl-substituted C₁ -C₁₀ -alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function, C₅ -C₇ -cycloalkyl or unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl,

with the proviso that the total number of carbon atoms present in the two radicals R¹ and R² is at least 7 when R¹ and R² are each C₁ -C₁₀ -alkyl or when one of R¹ and R² is C₁ -C₁₀ -alkyl and the other is C₅ -C₇ -cycloalkyl, and to a process for dyeing or printing textile materials.

U.S. Pat. No. 5,079,365 discloses thiazolemethinepyridone dyes (including the above-excepted dyes). There the dyes are used for transfer from a transfer to a plastic-coated paper by diffusion by means of an energy source. There is no mention there of these dyes also being suitable for dyeing or printing textile materials.

It is an object of the present invention to provide novel methine dyes which are advantageously suitable for use in the textile sector. The novel dyes shall have good fastness to dry heat setting and pleating and possess high brilliance.

We have found that this object is achieved by the pyridone dyes of the formula I more particularly described at the beginning.

Any alkyl or alkenyl appearing in the abovementioned formula I may be straight-chain or branched.

In substituted alkyl appearing in the abovementioned formula I the number of substituents is generally 1 or 2.

In substituted phenyl, furanyl or thienyl appearing in the abovementioned formula I the number of substituents is generally from 1 to 3, preferably 1 or 2.

R¹, R², R³, R⁴ and R⁶ are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, phenyl, 2-, 3- or 4-methylphenyl, 2-, 3- or 4-ethylphenyl, 2-, 3- or 4-propylphenyl, 2-, 3- or 4-isopropylphenyl, 2-, 3- or 4-butylphenyl, 2,3-, 2,4- or 2,6-dimethylphenyl, 2-, 3- or 4-methoxyphenyl, 2-, 3- or 4-ethoxyphenyl, 2,3-, 2,4- or 2,6-dimethoxyphenyl, 2-, 3- or 4-fluorophenyl, 2-, 3- or 4-chlorophenyl or 2-, 3- or 4-bromophenyl.

R¹, R², R³ and R⁶ may each also be for example pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, cyclopentyl, cyclohexyl or cycloheptyl.

R¹, R² and R⁶ may each also be for example benzyl, 1- or 2-phenylethyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3 ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl or 3,6,9,12-tetraoxatetradecyl.

R¹ and R² may each also be for example 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 2-propoxycarbonylethyl, 2-isopropoxycarbonylethyl, 2-butoxycarbonylethyl, 2- or 3-methoxycarbonylpropyl, 2- or 3-ethoxycarbonylpropyl, 2- or 3-propoxycarbonylpropyl, 2- or 3-butoxycarbonylpropyl, 2- or 4-methoxycarbonylbutyl, 2- or 4-ethoxycarbonylbutyl, 2- or 4-propoxycarbonylbutyl, 2- or 4-butoxycarbonylbutyl, 2-methoxycarbonyloxyethyl, 2-ethoxycarbonyloxyethyl, 2-propoxycarbonyloxyethyl, 2-isopropoxycarbonyloxyethyl, 2-butoxycarbonyloxyethyl, 2- or 3-methoxycarbonyloxypropyl, 2- or 3-ethoxycarbonyloxypropyl, 2- or 3-propoxycarbonyloxypropyl, 2- or 3-butoxycarbonyloxypropyl, 2- or 4-methoxycarbonyloxybutyl, 2- or 4-ethoxycarbonyloxybutyl, 2- or 4-propoxycarbonyloxybutyl, 2- or 4-butoxycarbonyloxybutyl, prop-1-en-3-yl, but-2-en-4-yl or 2-methylprop-1-en-3-yl.

R⁶ may also be for example 2-benzyloxyethyl, 2-(pyrazol-1-yl)-ethyl, 2- or 3-benzyloxypropyl, 2- or 3-(pyrazol-1-yl)propyl, 2- or 4-benzyloxybutyl, 2- or 4-(pyrazol-l-yl)butyl, 2-phenoxyethyl, 2- or 3-phenoxypropyl, 2- or 4-phenoxybutyl, 2-cyclohexyloxyethyl, 2- or 3-cyclohexyloxypropyl or 2- or 4-cyclohexyloxybutyl.

R³ may also be for example furan-2-yl, furan-3-yl, 3- or 4-methylfuran-2-yl, 3- or 4-chlorofuran-2-yl, thien-2-yl, thien-3-yl, 3- or 4-methylthien-2-yl or 3- or 4-chlorothien-2-yl.

R⁵ is for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, pentyloxycarbonyl, hexaloxycarbonyl, heptyloxycarbonyl, octyloxycarbonyl, 2-ethylhexyloxycarbonyl, mono- or dimethylcarbamoyl, mono- or diethylcarbamoyl, mono- or dipropylcarbamoyl, mono- or dibutylcarbamoyl, mono- or dipentylcarbamoyl, mono- or dihexylcarbamoyl, mono- or diheptylcarbamoyl, mono- or dioctylcarbamoyl, mono- or bis(2-ethylhexyl)carbamoyl or N-methyl-N-ethylcarbamoyl.

R¹ and R² combined together with the nitrogen atom joining them together to form a 5- or 6-membered saturated heterocyclic radical with or without further hetero atoms can be for example pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, thiomorpholinyl S,S-dioxide, piperazinyl or N-(C₁ -C₄ -alkyl)piperazinyl.

Preference is given to dyes wherein the total number of carbon atoms present in the two radicals R¹ and R² is at least 8 when R¹ and R² in formula I are each C₁ -C₁₀ -alkyl or when one of R¹ and R² is C₁ -C₁₀ -alkyl and the other is C₅ -C₇ -cycloalkyl.

Preference is further given to pyridone dyes of the formula I where X is nitrogen.

Preference is further given to pyridone dyes of the formula I where R⁴ is methyl.

Preference is further given to pyridone dyes of the formula I where R⁵ is cyano.

Preference is further given to pyridone dyes of the formula I where R³ is unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl or thienyl.

Preference is further given to pyridone dyes of the formula I where R⁶ is C₁ -C₈ -alkyl, cyclopentyl, cyclohexyl or unsubstituted or C₁ -C₄ -alkyl- or C₁ -C₄ -alkoxy-substituted phenyl.

Preference is further given to pyridone dyes of the formula I where R¹ and R² are each independently of the other C₁ -C₈ -alkyl, which may be C₁ -C₄ -alkoxy-, C₁ -C₄ -alkoxycarbonyl- or phenyl-substituted, cyclopentyl, cyclohexyl or prop-1-en-3-yl.

Particular preference is given to pyridone dyes of the formula I where R³ is phenyl or thienyl.

Particular preference is further given to pyridone dyes of the formula I where R⁶ is C₄ -C₈ -alkyl or cyclohexyl.

Particular preference is further given to pyridone dyes of the formula I where R¹ and R² are each independently of the other C₄ -C₈ -alkyl, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl, C₁ -C₄ -alkoxycarbonyl-C₂ -C₄ -alkyl, benzyl or prop-1-en-3-yl or where one of the two radicals R¹ and R² is C₁ -C₄ -alkyl and the other is cyclohexyl.

Very particular preference is given to pyridone dyes of the formula I where R¹ and R² are each independently of the other C₄ -C₈ -alkyl, benzyl or prop-1-en-3-yl.

The pyridone dyes of the formula I according to the invention can be prepared by methods known per se, for example by condensing an aldehyde of the formula II ##STR3## where X, R¹, R² and R³ are each as defined above, with a pyridone of the formula III ##STR4## where R⁴, R⁵ and R⁶ are each as defined above.

The present invention further provides a process for dyeing or printing textile materials, which comprises using pyridone dyes of the abovementioned formula I.

Preference is given to a process using dyes wherein the total number of carbon atoms present in the two radicals R¹ and R² is preferably at least 8 when R¹ and R² in formula I are each C₁ -C₁₀ -alkyl or when one of R¹ and R² is C₁ -C₁₀ -alkyl and the other is C₅ -C₇ -cycloalkyl.

Preference is further given to a process using pyridone dyes of the formula I where X is nitrogen.

Preference is further given to a process using pyridone dyes of the formula I where R⁴ is methyl.

Preference is further given to a process using pyridone dyes of the formula I where R⁵ is cyano.

Preference is further given to a process using pyridone dyes of the formula I where R³ is unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl or thienyl.

Preference is further given to a process using pyridone dyes of the formula I where R⁶ is C₁ -C₈ -alkyl, cyclopentyl, cyclohexyl or unsubstituted or C₁ -C₄ -alkyl- or C₁ -C₄ -alkoxy-substituted phenyl.

Preference is further given to a process using pyridone dyes of the formula I where R¹ and R² are each independently of the other C₁ -C₈ -alkyl, which is unsubstituted or C₁ -C₄ -alkoxy-, C₁ -C₄ -alkoxycarbonyl- or phenyl-substituted, cyclopentyl, cyclohexyl or prop-1-en-3-yl.

Particular preference is given to a process using pyridone dyes of the formula I where R³ is phenyl or thienyl.

Particular preference is further given to a process using pyridone dyes of the formula I where R⁶ is C₄ -C₈ -alkyl or cyclohexyl.

Particular preference is further given to a process using pyridone dyes of the formula I where R¹ and R² are each independently of the other C₄ -C₈ -alkyl, C₁ -C₄ -alkoxy-C₂ -C₄ -alkyl, C₁ -C₄ -alkoxycarbonyl-C₂ -C₄ -alkyl, benzyl or prop-1-en-3-yl or where one of the two radicals R¹ and R² is C₁ -C₄ -alkyl and the other is cyclohexyl.

Very particular preference is given to a process using pyridone dyes of the formula I where R¹ and R² are each independently of the other C₄ -C₈ -alkyl, benzyl or prop-1-en-3-yl.

For the purposes of the invention, textile materials are fibers, yarns, threads, knits, wovens or nonwovens composed of polyester, modified polyester, for example anionically modified polyester, or blend fabrics of polyesters with wool or cellulose derivatives, such as cotton or viscose. The dyeing and printing conditions are known per se. Details are also discernible from the Examples.

The novel pyridone dyes can be used as dye preparations. Such dye mixtures generally contain from 10 to 60% by weight, based on the weight of the dye preparation, of one or more of the pyridone dyes more particularly described at the beginning and from 40 to 90% by weight, based on the weight of the dye formulation, of dispersants, further assistants and/or water.

The novel pyridone dyes of the formula I yield brilliant dyeings in bluish red shades. The novel dyes are very strong and have good fastness to dry heat setting and pleating.

The Examples which follow illustrate the invention.

EXAMPLE 1 ##STR5##

9.8 g of 2-dibutylamino-4-phenyl-5-formylthiazole and 7.03 g of 1-hexyl-3-cyano-4-methyl-6-hydroxypyrid-2-one were suspended in 20 ml acetic anhydride. The reaction mixture was refluxed for 10 min at from 138° C. to 140° C. It was then cooled down. The dye precipitated at 50° C. To maintain stirrability, 100 ml of methanol were added. The precipitate was then filtered off with suction at room temperature, washed with methanol and subsequently dried.

Yield: 76% of theory; mp.: 145° C.

λ_(max) : 532 nm, in tetrahydrofuran (THF)

    ______________________________________                                         C.sub.31 H.sub.40 N.sub.4 O.sub.2 S (532.8)                                           C        H     N          O   S                                         ______________________________________                                         calc.    69.6       7.6   10.5     6.0 6.0                                     found    69.7       7.7   10.5     6.0 6.1                                     ______________________________________                                    

The same method gave the dyes listed individually below and also the dyes listed in Tables 1 and 2.

EXAMPLE 2 ##STR6##

mp.: 146° C.

Yield: 81% of theory

λ_(max) : 742 nm, in THF.

EXAMPLE 3 ##STR7##

mp.: 180° C.

Yield: 88% of theory

λ_(max) : 532 nm, in THF.

EXAMPLE 4 ##STR8##

mp.: 80° C.-85° C.

Yield: 76% of theory

λ_(max) : 741 nm, in THF.

EXAMPLE 5 ##STR9##

mp.: 121° C.

Yield: 50% of theory

λ_(max) : 529 nm, in THF.

EXAMPLE 6 ##STR10##

mp.: 157° C.

Yield: 70.4% of theory

λ_(max) : 741 nm, in THF.

EXAMPLE 7 ##STR11##

mp.: 180° C.

Yield: 82.5% of theory

λ_(max) : 537 nm, in THF.

EXAMPLE 8 ##STR12##

mp.: 203° C.

Yield: 89% of theory

λ_(max) : 537 nm, in THF.

EXAMPLE 9 ##STR13##

mp.: 174° C.

Yield: 88% of theory

λ_(max) : 537 nm, in THF.

EXAMPLE 10 ##STR14##

mp.: 149° C.

Yield: 74% of theory

λ_(max) : 537 nm, in THF.

                                      TABLE 1                                      __________________________________________________________________________      ##STR15##                                                                                                                       λmax  nm!             Ex. No.                                                                            L.sup.1   L.sup.2   L.sup.3    L.sup.4   mp.  °C.!                                                                    (in CH.sub.2 Cl.sub.2)       __________________________________________________________________________     11  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                            ##STR16##                                                                               >260 537                          12  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                            ##STR17##                                                                               158  537                          13  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                            ##STR18##                                                                               178  537                          14  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                            ##STR19##                                                                               143  537                          15  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                            ##STR20##                                                                               240  537                          16  C.sub.2 H.sub.5                                                                           ##STR21##                                                                               C.sub.6 H.sub.5                                                                            ##STR22##                                                                               207  537                          17  CH.sub.3                                                                                  ##STR23##                                                                               C.sub.6 H.sub.5                                                                            ##STR24##                                                                               221  534                          18  CH.sub.3                                                                                  ##STR25##                                                                               C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          227  534                          19  C.sub.2 H.sub.5                                                                           ##STR26##                                                                               C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          213  536                          20  C.sub.2 H.sub.5                                                                           ##STR27##                                                                               C.sub.6 H.sub.5                                                                           CH.sub.3  202  535                          21  C.sub.2 H.sub.5                                                                           ##STR28##                                                                               C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                         202  535                          22  iso-C.sub.4 H.sub.9                                                                      iso-C.sub.4 H.sub.9                                                                      C.sub.6 H.sub.5                                                                           204       537                               23  iso-C.sub.4 H.sub.9                                                                      iso-C.sub.4 H.sub.9                                                                      C.sub.6 H.sub.5                                                                           CH.sub.3  220  535                          24  sec-C.sub.4 H.sub.9                                                                      sec-C.sub.4 H.sub.9                                                                      C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          160  540                          25  sec-C.sub.4 H.sub.9                                                                      sec-C.sub.4 H.sub.9                                                                      C.sub.6 H.sub.5                                                                           CH.sub.3  219  538                          26  CH.sub.2 C.sub.6 H.sub.5                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                 C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                         198  531                          27  C.sub.2 H.sub.5                                                                          C.sub.2 H.sub.4 COOC.sub.4 H.sub.9                                                        ##STR29## C.sub.4 H.sub.9                                                                          174  532                          28                                                                                  ##STR30##                                                                                ##STR31##                                                                               C.sub.6 H.sub.5                                                                           CH.sub.3  128  538                          29                                                                                  ##STR32##                                                                                ##STR33##                                                                               C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                           89  539                          30  CH.sub.2 CHCH.sub.2                                                                      CH.sub.2 CHCH.sub.2                                                                      C.sub.6 H.sub.5                                                                           CH.sub.3  194  533                          31  CH.sub.2 CHCH.sub.2                                                                      CH.sub.2 CHCH.sub.2                                                                      C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          172  532                          32                                                                                  ##STR34##                                                                                ##STR35##                                                                               C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                         63-65                                                                               539                          33  CH.sub.2 CHCH.sub.2                                                                      CH.sub.2 CHCH.sub.2                                                                       ##STR36## CH.sub.3  224  534                          34  CH.sub.2 CHCH.sub.2                                                                      CH.sub.2 CHCH.sub.2                                                                       ##STR37## C.sub.4 H.sub.9                                                                          169  534                          35  CH.sub.2 CHCH.sub.2                                                                      CH.sub.2 CHCH.sub.2                                                                       ##STR38## C.sub.6 H.sub.13                                                                         180  533                          36  (CH.sub.2).sub.4    C.sub.6 H.sub.5                                                                           CH.sub.3  >255 534                          37  (CH.sub.2).sub.4    C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          251  534                          38  (CH.sub.2).sub.4    C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                         115  533                          39  C.sub.2 H.sub.4 OCH.sub.3                                                                C.sub.2 H.sub.4 OCH.sub.3                                                                C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                         180  533                          40  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR39## C.sub.4 H.sub.9                                                                          182  542                          41  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR40## C.sub.6 H.sub.13                                                                         161  542                          42  CH.sub.2 C.sub.6 H.sub.5                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                 C.sub.6 H.sub.5                                                                           CH.sub.3  225  533                          43  CH.sub.2 C.sub.6 H.sub.5                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                 C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          214  533                          44  C.sub.5 H.sub.11                                                                         C.sub.5 H.sub.11                                                                         C.sub.6 H.sub.5                                                                           CH.sub.3  151  537                          45  C.sub.5 H.sub.11                                                                         C.sub.5 H.sub.11                                                                         C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          168  537                          46  C.sub.5 H.sub.11                                                                         C.sub.5 H.sub.11                                                                         C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                         117  537                          47  C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                          163  537                          48  C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                         138  537                          49  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                            ##STR41##                                                                               163  538                          50  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                           C.sub.3 H.sub.6 OCH.sub.2 C.sub.6                                              H.sub.5   125  538                          51  C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.5                                                                               539                          52  C.sub.2 H.sub.4 OCH.sub.3                                                                C.sub.2 H.sub.4 OCH.sub.3                                                                C.sub.6 H.sub.5                                                                           CH.sub.3  215  534                          53  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                               536                          54  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR42## C.sub.6 H.sub.13                                                                              555                          55  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.3                                                                         CH.sub.3       534                          1.  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.3                                                                         C.sub.4 H.sub.9                                                                               534                          2.  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.3                                                                         C.sub.6 H.sub.13                                                                              534                          3.  C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                               C.sub.6 H.sub.5                                                                           CH.sub.3       534                          4.  C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                               C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                               532                          5.  C.sub.2 H.sub.5                                                                          C.sub.3 H.sub.6 OC.sub.2 H.sub.4 OCH.sub.3                                               C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                              534                          6.  C.sub.2 H.sub.4 O(C.sub.2 H.sub.4 O).sub.2 CH.sub.3                                      C.sub.2 H.sub.4 O(C.sub.2 H.sub.4 O).sub.2 CH.sub.3                                      C.sub.6 H.sub.5                                                                           CH.sub.3       531                          7.  C.sub.2 H.sub.4 O(C.sub.2 H.sub.4 O).sub.2 CH.sub.3                                      C.sub.2 H.sub.4 O(C.sub.2 H.sub.4 O).sub.2 CH.sub.3                                      C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                               532                          8.  C.sub.2 H.sub.4 O(C.sub.2 H.sub.4 O).sub.2 CH.sub.3                                      C.sub.2 H.sub.4 O(C.sub.2 H.sub.4 O).sub.2 CH.sub.3                                      C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                              533                          9.  C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          CH(CH.sub.3).sub.2                                                                        C.sub.6 H.sub.13                                                                              527                          10. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          CH(CH.sub.3).sub.2                                                                        C.sub.4 H.sub.9                                                                               528                          11. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          CH(CH.sub.3).sub.2                                                                        CH.sub.3       526                          12. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR43## CH.sub.3       529                          13. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR44## C.sub.4 H.sub.9                                                                               529                          14. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR45## C.sub.6 H.sub.13                                                                              529                          15. C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.13                                                                          ##STR46## CH.sub.3       529                          16. C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.13                                                                          ##STR47## C.sub.4 H.sub.9                                                                               529                          17. C.sub.6 H.sub.13                                                                         C.sub.6 H.sub.13                                                                          ##STR48## C.sub.6 H.sub.13                                                                              529                          18. CH(CH.sub.3).sub.2                                                                        ##STR49##                                                                               C.sub.6 H.sub.5                                                                           C.sub.4 H.sub.9                                                                               533                          19. CH(CH.sub.3).sub.2                                                                        ##STR50##                                                                               C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                              533                          20. C.sub.2 H.sub.5                                                                           ##STR51##                                                                               C.sub.6 H.sub.5                                                                           C.sub.6 H.sub.13                                                                              534                          21. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.3 H.sub.7                                                                           CH.sub.3       527                          22. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR52## CH.sub.3       528                          23. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR53## C.sub.4 H.sub.9                                                                               529                          24. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.3 H.sub.7                                                                           C.sub.6 H.sub.13                                                                              528                          25. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                        CH.sub.3       526                          26. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                           ##STR54## C.sub.6 H.sub.13                                                                              528                          27. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                        C.sub.6 H.sub.13                                                                              527                          28. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.3                                                                         C.sub.2 H.sub.4 OCH.sub.3                                                                     535                          29. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C(CH.sub.3).sub.3                                                                         C.sub.3 H.sub.6 OCH.sub.3                                                                     534                          30. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                           C.sub.2 H.sub.4 OCH.sub.3                                                                     538                          31. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          C.sub.6 H.sub.5                                                                           C.sub.3 H.sub.6 OCH.sub.3                                                                     538                          32. C.sub.4 H.sub.9                                                                          C.sub.4 H.sub.9                                                                          CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                                        C.sub.4 H.sub.9                                                                               527                          33. CH.sub.2 C.sub.6 H.sub.5                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                 C(CH.sub.3).sub.3                                                                         CH.sub.3       530                          34. CH.sub.2 C.sub.6 H.sub.5                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                 C(CH.sub.3).sub.3                                                                         C.sub.4 H.sub.9                                                                               531                          35. CH.sub.2 C.sub.6 H.sub.5                                                                 CH.sub.2 C.sub.6 H.sub.5                                                                 C(CH.sub.3).sub.3                                                                         C.sub.6 H.sub.13                                                                              531                          __________________________________________________________________________

                                      TABLE 2                                      __________________________________________________________________________      ##STR55##                                                                     Bsp.                                         λmax  nm!                  Nr.                                                                               L.sup.1                                                                             L.sup.2                                                                             L.sup.3                                                                             X   L.sup.4  L.sup.5    L.sup.6                                                                           (in CH.sub.2 Cl.sub.2)            __________________________________________________________________________     91 C.sub.4 H.sub.9                                                                     C.sub.4 H.sub.9                                                                     C.sub.6 H.sub.5                                                                     N   CH.sub.3 CONHCH.sub.3                                                                              CH.sub.3                                                                          520                               92 sec-C.sub.4 H.sub.9                                                                 sec-C.sub.4 H.sub.9                                                                 C.sub.6 H.sub.5                                                                     N   CH.sub.3 CONHCH.sub.3                                                                              H  551                               93 C.sub.4 H.sub.9                                                                     C.sub.4 H.sub.9                                                                     C(CH.sub.3).sub.3                                                                   N   CH.sub.3 CONHCH.sub.3                                                                              CH.sub.3                                                                          524                               94 C.sub.4 H.sub.9                                                                     C.sub.4 H.sub.9                                                                     C(CH.sub.3).sub.3                                                                   N   CH.sub.3                                                                                 ##STR56## CH.sub.3                                                                          552                               95 C.sub.4 H.sub.9                                                                     C.sub.4 H.sub.9                                                                     C.sub.6 H.sub.5                                                                     N   CH.sub.3 CN         H  545                               96 sec-C.sub.4 H.sub.9                                                                 sec-C.sub.4 H.sub.9                                                                 C.sub.6 H.sub.5                                                                     N   CH.sub.3 CN         H  558                               97 C.sub.4 H.sub.9                                                                     C.sub.4 H.sub.9                                                                     C.sub.6 H.sub.5                                                                     N   C.sub.6 H.sub.13                                                                        CN         H  553                               98 C.sub.4 H.sub.9                                                                     C.sub.4 H.sub.9                                                                     C.sub.6 H.sub.5                                                                     N   CH.sub.2 CH(C.sub.2 H.sub.5)C.sub.4 H.sub.9                                             CN         H  550                               99 C.sub.4 H.sub.9                                                                     C.sub.4 H.sub.9                                                                     C(CH.sub.3).sub.3                                                                   CCN C.sub.2 H.sub.5                                                                         CN         CH.sub.3                                                                          559                               __________________________________________________________________________

Dyeing method

5 g of polyester fabric (PES) are introduced at 50° C. into 100 ml of a dyeing liquor which contains a below-specified dye and whose pH has been set to 4.5 with acetic acid/sodium acetate. After 5 minutes at 50° C. the liquor is raised to 130° C., held at that temperature for 45 minutes and then cooled down to 70° C. over 20 minutes.

Thereafter the dyed polyester fabric is reduction cleared by treating it for 15 minutes at 70° C. in 200 ml of liquor containing 5 ml/l of 32% strength by weight sodium hydroxide solution, 3 g/l of sodium dithionite and 1 g/l of an addition product of 48 mol of ethylene oxide with 1 mol of castor oil. Finally the fabric is rinsed, neutralized with dilute acetic acid, rinsed once more and dried.

The dyes of Examples 1 to 10 and 19 were dyed up by the above dyeing method. Very strong dyeings were obtained in brilliant bluish red shades. 

We claim:
 1. Pyridone dyes of the formula I ##STR57## where X is nitrogen or C--CN,R¹ and R² are identical or different and each is independently of the other unsubstituted or C₁ -C₄ -alkoxycarbonyl-, C₁ -C₄ -alkoxycarbonyloxy- or phenyl-substituted C₁ -C₁₀ -alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function, C₅ -C₇ -cycloalkyl, C₃ -C₄ -alkenyl, unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl, or R¹ and R² are together with the nitrogen atom joining them together a 5- or 6-membered saturated heterocyclic radical with or without further hetero atoms, R³ is hydrogen, C₁ -C₁₀ -alkyl, C₅ -C₇ -cycloalkyl, or benzyl, R⁴ is hydrogen, C₁ -C₄ -alkyl or unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl, R⁵ is cyano, carbamoyl, mono- or di(C₁ -C₈ -alkyl)carbamoyl, carboxyl, C₁ -C₈ -alkoxycarbonyl or benzimidazolyl, and R⁶ is unsubstituted or phenyl-, phenoxy-, cyclohexyloxy- or pyrazolyl-substituted C₁ -C₁₀ -alkyl with or without interruption by from 1 to 4 oxygen atoms in ether function, C₅ -C₇ -cycloalkyl or unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl,with the proviso that the total number of carbon atoms present in the two radicals R¹ and R² is at least 7 when R¹ and R² are each C₁ -C₁₀ -alkyl or when one of R¹ and R² is C₁ -C₁₀ -alkyl and the other is C₅ -C₇ -cycloalkyl.
 2. Pyridone dyes as claimed in claim 1, wherein X is nitrogen.
 3. Pyridone dyes as claimed in claim 1, wherein R⁴ is methyl.
 4. Pyridone dyes as claimed in claim 1, wherein R³ is unsubstituted or C₁ -C₄ -alkyl-, C₁ -C₄ -alkoxy- or halogen-substituted phenyl or thienyl.
 5. Pyridone dyes as claimed in claim 1, wherein R⁶ is C₁ -C₈ -alkyl, cyclopentyl, cyclohexyl or unsubstituted or C₁ -C₄ -alkyl- or C₁ -C₄ -alkoxy-substituted phenyl.
 6. Pyridone dyes as claimed in claim 1, wherein R³ is hydrogen.
 7. Pyridone dyes as claimed in claim 1, wherein R³ is C₁ -C₁₀ -alkyl.
 8. Pyridone dyes as claimed in claim 1, wherein R³ is C₅ -C₇ -cycloalkyl.
 9. Pyridone dyes as claimed in claim 1, wherein R³ is benzyl.
 10. A process for dyeing or printing a textile material, which comprises applying to said textile material a pyridone dye as claimed in claim
 1. 